Sodium Hydroxide → 3-Bromo-5-chloropyridin-2-amine

HRID 1828760Notes

Reaction equation

HRID 1828760 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[Br:9]Br.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([Br:9])=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 661742-Amino-5-chloropyridine

Product 1

HCID 27639713-Bromo-5-chloropyridin-2-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-chloropyridine (10 g) in acetic acid (75 mL) at r.t. was added bromine (2.6 mL) slowly. After 30 min, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0° C. The resulting orange precipitate was dissolved in ethyl acetate and washed successively with saturated potassium carbonate, saturated Na2S2O3 and brine, dried and concentrated. Flash chromatography (eluting with hexane/ethyl acetate, 3:1 v/v) of the residual solid provided the title compound as a pale yellow solid (14.8 g).

Workup

  1. washwashed successively with saturated potassium carbonate, saturated Na2S2O3 and brine
  2. customdried
  3. concentrationconcentrated
  4. washFlash chromatography (eluting with hexane/ethyl acetate, 3:1 v/v) of the residual solid

Sources & evidence

ORD record
ord-5a18f315c88d4317884264cd35f8f285
Source dataset
uspto-grants-2006_06
Patent number
US07060715B2

Reaction notes

Loading…